#------------------------------------------------------------------------------
#$Date: 2022-03-30 03:22:27 +0300 (Wed, 30 Mar 2022) $
#$Revision: 274092 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/86/7158609.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7158609
loop_
_publ_author_name
'Chernykh, Anton V.'
'Chernykh, Alla V.'
'Radchenko, Dmytro S.'
'Chheda, Pratik Rajesh'
'Rusanov, Eduard B.'
'Grygorenko, Oleksandr O.'
'Spies, M. Ashley'
'Volochnyuk, Dmitriy M.'
'Komarov, Igor V.'
_publ_section_title
;
 A stereochemical journey around spirocyclic glutamic acid analogs
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D2OB00146B
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H26 N2 O3 S'
_chemical_formula_sum            'C16 H26 N2 O3 S'
_chemical_formula_weight         326.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/4
_audit_update_record
;
2021-09-08 deposited with the CCDC.	2022-03-03 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.0729(19)
_cell_length_b                   9.1807(18)
_cell_length_c                   28.272(6)
_cell_measurement_reflns_used    826
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      19.84
_cell_measurement_theta_min      2.33
_cell_volume                     1835.8(7)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            19832
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.332
_exptl_absorpt_coefficient_mu    0.189
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.50
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.181
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.560
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Flack x determined using 969 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     206
_refine_ls_number_reflns         3753
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0707
_refine_ls_R_factor_gt           0.0492
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0339P)²+0.6714P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1010
_refine_ls_wR_factor_ref         0.1110
_reflns_Friedel_coverage         0.718
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2940
_reflns_number_total             3753
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ob00146b2.cif
_cod_data_source_block           xray74[62B]
_cod_database_code               7158609
_shelx_shelxl_version_number     2016/4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.901
_shelx_estimated_absorpt_t_max   0.994
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S -0.34700(13) 0.20576(10) 0.92947(3) 0.0366(2) Uani 1 1 d . . . . .
O1 O -0.4404(4) 0.2609(3) 0.97270(9) 0.0551(8) Uani 1 1 d . . . . .
O2 O 0.6012(4) -0.1214(4) 0.80132(9) 0.0584(9) Uani 1 1 d . . . . .
O3 O 0.3179(5) -0.0943(5) 0.77000(11) 0.0966(15) Uani 1 1 d . . . . .
N1 N -0.1247(4) 0.1567(3) 0.94118(9) 0.0304(7) Uani 1 1 d . . . . .
H1N H -0.073(5) 0.212(4) 0.9656(13) 0.042(10) Uiso 1 1 d . . . . .
N2 N -0.2897(8) -0.1028(5) 1.01964(16) 0.0955(18) Uani 1 1 d . . . . .
C1 C -0.0932(6) 0.0016(4) 0.94930(12) 0.0409(9) Uani 1 1 d . . . . .
C2 C 0.1211(6) -0.0312(5) 0.94980(12) 0.0505(11) Uani 1 1 d . . . . .
H2A H 0.201132 0.055465 0.955597 0.061 Uiso 1 1 calc R U . . .
H2B H 0.157242 -0.112824 0.970803 0.061 Uiso 1 1 calc R U . . .
C3 C 0.1045(6) -0.0737(4) 0.89712(13) 0.0413(10) Uani 1 1 d . . . . .
C4 C -0.1091(6) -0.0867(4) 0.90303(14) 0.0464(10) Uani 1 1 d . . . . .
H4A H -0.153880 -0.187832 0.907640 0.056 Uiso 1 1 calc R U . . .
H4B H -0.182365 -0.036967 0.877924 0.056 Uiso 1 1 calc R U . . .
C5 C 0.2309(6) -0.1927(5) 0.87616(14) 0.0568(12) Uani 1 1 d . . . . .
H5A H 0.166129 -0.255443 0.852755 0.068 Uiso 1 1 calc R U . . .
H5B H 0.297423 -0.251938 0.900215 0.068 Uiso 1 1 calc R U . . .
C6 C 0.3551(6) -0.0729(5) 0.85373(13) 0.0524(11) Uani 1 1 d . . . . .
H6 H 0.463727 -0.047157 0.874764 0.063 Uiso 1 1 calc R U . . .
C7 C 0.1880(5) 0.0329(4) 0.86094(13) 0.0428(10) Uani 1 1 d . . . . .
H7A H 0.225076 0.127995 0.874629 0.051 Uiso 1 1 calc R U . . .
H7B H 0.108743 0.046282 0.832412 0.051 Uiso 1 1 calc R U . . .
C8 C 0.4192(6) -0.0966(5) 0.80395(14) 0.0516(11) Uani 1 1 d . . . . .
C9 C 0.6833(6) -0.1485(6) 0.75460(14) 0.0587(13) Uani 1 1 d . . . . .
H9 H 0.587770 -0.196490 0.733688 0.070 Uiso 1 1 calc R U . . .
C10 C 0.7396(11) -0.0056(7) 0.73418(19) 0.095(2) Uani 1 1 d . . . . .
H10A H 0.795151 -0.020704 0.702809 0.143 Uiso 1 1 calc R U . . .
H10B H 0.627962 0.057067 0.731391 0.143 Uiso 1 1 calc R U . . .
H10C H 0.832737 0.041059 0.754900 0.143 Uiso 1 1 calc R U . . .
C11 C 0.8462(8) -0.2486(7) 0.76254(18) 0.092(2) Uani 1 1 d . . . . .
H11A H 0.906845 -0.270562 0.732205 0.138 Uiso 1 1 calc R U . . .
H11B H 0.937807 -0.201934 0.783659 0.138 Uiso 1 1 calc R U . . .
H11C H 0.800882 -0.339175 0.776982 0.138 Uiso 1 1 calc R U . . .
C12 C -0.2037(7) -0.0547(5) 0.98946(16) 0.0602(13) Uani 1 1 d . . . . .
C13 C -0.2985(6) 0.3649(4) 0.89286(13) 0.0479(11) Uani 1 1 d . . . . .
C14 C -0.4909(8) 0.4320(7) 0.88308(19) 0.090(2) Uani 1 1 d . . . . .
H14A H -0.551952 0.457407 0.913093 0.136 Uiso 1 1 calc R U . . .
H14B H -0.569814 0.361900 0.865952 0.136 Uiso 1 1 calc R U . . .
H14C H -0.475150 0.520099 0.863895 0.136 Uiso 1 1 calc R U . . .
C15 C -0.2109(7) 0.3105(6) 0.84759(14) 0.0709(15) Uani 1 1 d . . . . .
H15A H -0.082512 0.275586 0.853951 0.106 Uiso 1 1 calc R U . . .
H15B H -0.206048 0.390069 0.824507 0.106 Uiso 1 1 calc R U . . .
H15C H -0.287352 0.230556 0.834867 0.106 Uiso 1 1 calc R U . . .
C16 C -0.1676(10) 0.4687(5) 0.91872(18) 0.0877(19) Uani 1 1 d . . . . .
H16A H -0.222315 0.493421 0.949544 0.132 Uiso 1 1 calc R U . . .
H16B H -0.151677 0.557656 0.899978 0.132 Uiso 1 1 calc R U . . .
H16C H -0.044334 0.422143 0.923356 0.132 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 S1 N1 110.44(16) . . ?
O1 S1 C13 106.20(18) . . ?
N1 S1 C13 98.73(17) . . ?
C8 O2 C9 118.1(3) . . ?
C1 N1 S1 116.0(2) . . ?
N1 C1 C12 112.5(3) . . ?
N1 C1 C4 111.6(3) . . ?
C12 C1 C4 115.5(3) . . ?
N1 C1 C2 110.0(3) . . ?
C12 C1 C2 116.5(4) . . ?
C4 C1 C2 88.7(3) . . ?
C3 C2 C1 88.0(3) . . ?
C4 C3 C5 124.5(4) . . ?
C4 C3 C7 120.3(3) . . ?
C5 C3 C7 88.4(3) . . ?
C4 C3 C2 89.4(3) . . ?
C5 C3 C2 120.6(3) . . ?
C7 C3 C2 116.9(3) . . ?
C3 C4 C1 88.8(3) . . ?
C3 C5 C6 89.0(3) . . ?
C8 C6 C7 116.7(4) . . ?
C8 C6 C5 117.1(4) . . ?
C7 C6 C5 87.6(3) . . ?
C3 C7 C6 88.9(3) . . ?
O3 C8 O2 123.1(4) . . ?
O3 C8 C6 124.8(4) . . ?
O2 C8 C6 112.2(3) . . ?
O2 C9 C10 107.8(4) . . ?
O2 C9 C11 106.0(4) . . ?
C10 C9 C11 113.3(5) . . ?
N2 C12 C1 177.6(5) . . ?
C15 C13 C16 111.5(4) . . ?
C15 C13 C14 110.4(4) . . ?
C16 C13 C14 112.3(4) . . ?
C15 C13 S1 107.1(3) . . ?
C16 C13 S1 110.2(3) . . ?
C14 C13 S1 105.1(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.478(3) . ?
S1 N1 1.669(3) . ?
S1 C13 1.823(4) . ?
O2 C8 1.309(5) . ?
O2 C9 1.464(5) . ?
O3 C8 1.198(5) . ?
N1 C1 1.459(5) . ?
N2 C12 1.137(5) . ?
C1 C12 1.473(6) . ?
C1 C4 1.543(5) . ?
C1 C2 1.545(6) . ?
C2 C3 1.544(5) . ?
C3 C4 1.525(5) . ?
C3 C5 1.531(5) . ?
C3 C7 1.534(6) . ?
C5 C6 1.543(6) . ?
C6 C8 1.495(5) . ?
C6 C7 1.543(5) . ?
C9 C10 1.488(7) . ?
C9 C11 1.490(7) . ?
C13 C15 1.507(5) . ?
C13 C16 1.516(7) . ?
C13 C14 1.520(6) . ?
